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John DeMato Blog

Welcome to the Deliver Magic blog, where experts who speak, coach, train, consult, and write books will find actionable insights to elevate their personal brands through visual storytelling. From strategy tips and branding photography to live event coverage and storytelling techniques, discover step-by-step guides designed to help you align what you say with how you show up in photos. Get ready to unlock the magic behind creating a cohesive visual identity that drives engagement, builds credibility, and inspires your audience. #DeliverMagic

The must-have ingredient for headshots

 

You can have all the fancy camera gear in the world…

 
 

…but if you’re missing one key ingredient in your session, the photos are unusable.

 

Recently, I decided to grace my camera’s presence with my own face.

The last time I took a professional headshot was in 2015, which, quite frankly, is a sin, I know. 

I bitch at my clients for using outdated photos, and here I am being Mr. Hypocrite!

Part of the reason why it’s taken so long is because, well, it’s a pain in the ass to shoot one of my headshots without a photographer behind the camera. 

Regardless of my hemming and hawing, I finally decided to fix that problem.

So, I packed a bag of remotes, cables, triggers, a monitor, and alongside my camera, light and tripod, I lugged all this crap down to the street level outside my apartment building and set up shop. 

Within minutes, I locked in the look and frame of the photo. 

I snapped a couple shots and, while the headshots technically were on point, there was something missing:

My facial expressions missed the mark:

Whether my mouth looked uncomfortable, or my eyes looked weird and creepy, the one constant throughout was that each and every photo felt unnatural and disingenuous…

Not a good look for a headshot, let alone ANY photo, for that matter. 

The goal for every headshot session is to capture a natural expression that conveys confidence, approachability, and likability. 

And these photos were dropping the ball. 

I took about 65 photos that all kinda looked and felt ehhhhh, and was a bit unsure if I was going to be able to capture something I’d be proud to share…

…and then, my super and a neighbor popped out of the building to check out what I was doing. 

Once they came by, I knew my problem would be solved. 

I started chatting with them and reacting to what they were saying - all the while, snapping shots with the remote trigger in my hand. 

I’d provoke them into saying things that would make my face move around to produce more genuine expressions. 

They didn’t realize that I was directing them to help me, but they came up big in this moment.

At one point, my neighbor started doing some wacky thing with his arms while holding his dog’s leash, and, after I made a snarky remark about that, I snapped this shot:

After I checked the photo on the back of the camera, I knew this was the keeper and my work was done. 

If it weren’t for them, I’d probably still be outside in my shorts and flip-flops - doesn’t matter what you’re wearing outside the frame of the shot, :) - trying to nail a photo.

How did they make the difference? 

Rapport.

Since I didn’t have someone behind the camera shepherding me through the process, I, at first, was trying to make myself laugh by thinking of different things. To the many passersby on the street and in their cars at the light, I must’ve looked crazy laughing and talking to myself. 

I certainly looked like it in many of the photos I captured. 

Once I had someone that I trust and like to chat with, the game completely changed, and I was able to capture a natural expression that encapsulates my personality to a T.

That’s why it’s important for you to not only work with a photographer who uses fancy gear and has a great eye, but they have the ability to communicate with you in a way that places you in a comfort zone to be yourself in front of the camera.

Keep that in mind the next time you’re looking to hire a photographer.

Look beyond the work, and qualify whether or not this person has the ability to create a rapport that leads to magical photos. 

Over to you…

Have you gone through a headshot session where the photos technically looked wonderful, but your expression left much to be desired? Please share your story in the comment section below.